Tetrahydrofuran → 6-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid

HRID 2406764Notes

Reaction equation

[OH-].[Na+].O1CCCC1.[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[N:37][CH:36]=2)[N:24]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CO>[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[N:37][CH:36]=2)[N:24]=1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 65 °C

Procedure

A 1N sodium hydroxide aqueous solution (2 ml) was added to a solution of tetrahydrofuran (2 ml) and methanol (2 ml) containing methyl 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinate (75 mg), followed by stirring at 65° C. for 2 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled away under reduced pressure. A saturated aqueous ammonium chloride solution was added to the obtained residue, solid matter was collected by filtration and washed with water and ethyl acetate, and a yellow solid of 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid (67 mg) was thus obtained.

Workup

temperatureThe reaction mixture was cooled to room temperature
distillationthe solvent was distilled away under reduced pressure
additionA saturated aqueous ammonium chloride solution was added to the obtained residue, solid matter
filtrationwas collected by filtration
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-f0d2f03db4fc4301a2a456bd7442bb1d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809371B2

Reaction notes

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